(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester

Base Information

• Chemical Name: (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester
• CAS No.: 215797-95-8
• Molecular Formula: C₂₆H₄₃NO₈Si
• Molecular Weight: 525.715
• Mol file: 215797-95-8.mol

Synonyms:(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester

Chemical Property of (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester

There total 7 articles about (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(2R,3R,4S)-2-Benzyl-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid (S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl ester (215797-99-2) → (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester (215797-95-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; at 25 ℃; for 14h; under 3040 Torr;

DOI:10.1016/S0040-4020(98)00777-7

Reference yield:

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one (96837-44-4) → (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester (215797-95-8)

Guidance literature:

Multi-step reaction with 5 steps

2: 100 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 13 h / 25 °C

3: 89 percent / imidazole / dimethylformamide / 6 h / 25 °C

4: 56 percent / DMAP, EDCI*HCl / CH₂Cl₂ / 21 h / 25 °C

5: 100 percent / H₂ / Pd(OH)2/C / ethanol / 14 h / 25 °C / 3040 Torr

With 1H-imidazole; dmap; lithium hydroxide; hydrogen; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00777-7

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid (2S)-2-tert-butoxycarbonylamino-2-carboxyethyl ester (215797-95-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / n-butyllithium / tetrahydrofuran / 3 h / -78 °C

3: 100 percent / aq. H₂O₂, LiOH / tetrahydrofuran / 13 h / 25 °C

4: 89 percent / imidazole / dimethylformamide / 6 h / 25 °C

5: 56 percent / DMAP, EDCI*HCl / CH₂Cl₂ / 21 h / 25 °C

6: 100 percent / H₂ / Pd(OH)2/C / ethanol / 14 h / 25 °C / 3040 Torr

With 1H-imidazole; dmap; lithium hydroxide; n-butyllithium; hydrogen; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00777-7

upstream raw materials:

(2R,3R,4S)-2-Benzyl-4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid (S)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl ester

tert-butyldimethylsilyl chloride

(R)-4-isopropyl-3-(3-phenylpropanoyl)oxazolidin-2-one

hydrocinnamic acid chloride

Downstream raw materials:

(3R,4R,5S)-3-benzyl-4-(tert-butyldimethylsilanyloxy)-5-methyldihydrofuran-2-one

(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one